2-Ethyl-2,3-dihydro-1,2-benzothia­zole-1,1,3-trione

Khan, M.H.; Khan, I.U.; Arshad, M.N.; Akkurt, M.

doi:10.1107/S1600536811009184

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o887

doi:10.1107/S1600536811009184

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2-Ethyl-2,3-dihydro-1,2-benzothiazole-1,1,3-trione

Muneeb Hayat Khan,^a Islam Ullah Khan,^a ^* Muhammad Nadeem Arshad ^a and Mehmet Akkurt ^b ^*

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: iukhan@gcu.edu.pk, akkurt@erciyes.edu.tr

(Received 9 March 2011; accepted 10 March 2011; online 15 March 2011)

In the title molecule, C₉H₉NO₃S, the bond lengths and angles fall within normal ranges. All nine ring atoms almost lie in a common plane (r.m.s. deviation 0.021 Å). In the crystal, symmetry-related molecules are linked via C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For related literature on benzisothiazolone-1,1-dioxide derivatives, see: Hu et al. (2004 ); Kap-Sun & Nicholas (1998 ); Liang et al. (2006 ); Masashi et al. (1999 ); Nagasawa et al. (1995 ). For related structures, see: Hu et al. (2006 ); Xu et al. (2005 ); Wen et al. (2006 ).

Experimental

Crystal data

C₉H₉NO₃S
M_r = 211.24
Monoclinic, P 2₁ /n
a = 10.4559 (5) Å
b = 7.5484 (5) Å
c = 12.9408 (7) Å
β = 105.863 (2)°
V = 982.46 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 K
0.19 × 0.18 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
9319 measured reflections
2429 independent reflections
1822 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.144
S = 1.08
2429 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.37	3.265 (2)	162
C3—H3⋯O2ⁱⁱ	0.93	2.53	3.295 (3)	140
C8—H8A⋯O3ⁱⁱⁱ	0.97	2.45	3.139 (3)	128
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009184/bt5490sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009184/bt5490Isup2.hkl

checkCIF report

Comment top

Benzisothiazolone-1,1-dioxide is part of a class of heterocycles which has been investigated in pharmaceutical research (Kap-Sun & Nicholas, 1998). 1,2-Benzisothiazole-3-one 1,1-dioxide (saccharin) has been widely incorporated into a variety of biologically active compounds. It has been identified as an important molecular component in various classes of 5-Htla antagonists, analgesics and human mast cell tryptase inhibitors (Liang et al., 2006). In particular, N-substituted derivatives, e.g with N-hydroxy and N-alkyl substituents, have shown important biological activity (Nagasawa et al., 1995). Among N-alkyl derivatives, various synthetic routes have been reported for the synthesis of the title compound involving ionic liquids and free radical mechanisms (Hu et al., 2004; Masashi et al., 1999).

In the molecule of the title compound (Fig. 1), all the bond lengths and bond angles agree with the corresponding values in similar structures containing benzisothiazole group (Hu et al., 2006; Xu et al., 2005; Wen et al., 2006).

Atoms C1–C7, S1, O1 and N1 of the title molecule are essentially coplanar, with a maximum deviation of 0.020 (1) Å for S1. The packing of the molecules is stabilized by intermolecular C—H···O intermolecular hydrogen bonds (Table 1, Fig. 2).

Related literature top

For related literature on benzisothiazolone-1,1-dioxide derivatives, see: Hu et al. (2004); Kap-Sun & Nicholas (1998); Liang et al. (2006); Masashi et al. (1999); Nagasawa et al. (1995). For related structures, see: Hu et al. (2006); Xu et al. (2005); Wen et al. (2006).

Experimental top

Sodium sacharrin (0.5 g, 2.439 mmol) was taken in round bottom flask and 20 ml DMF was added to it. It was kept for stirring at room temperature for 5 minutes then ethyl iodide (0.195 ml, 2.439 mmol) was added to the solution. Then reaction mixture was kept under reflux for 3 h at 333 K and after 3 h the TLC confirmed the completion of reaction. The product was obtained in ice-water, filtered and dried. Dried precipitates were dissolved in methanol for crystallization (yield: 93%).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title molecule with atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. A view of the packing and hydrogen bonding interactions of the title compound down the b axis. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

2-Ethyl-2,3-dihydro-1,2-benzothiazole-1,1,3-trione top

Crystal data top

C₉H₉NO₃S	F(000) = 440
M_r = 211.24	D_x = 1.428 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3812 reflections
a = 10.4559 (5) Å	θ = 2.7–28.3°
b = 7.5484 (5) Å	µ = 0.31 mm⁻¹
c = 12.9408 (7) Å	T = 296 K
β = 105.863 (2)°	Plate, colourless
V = 982.46 (10) Å³	0.19 × 0.18 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1822 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.081
Graphite monochromator	θ_max = 28.3°, θ_min = 3.2°
ϕ and ω scans	h = −13→13
9319 measured reflections	k = −10→10
2429 independent reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0789P)² + 0.0563P] where P = (F_o² + 2F_c²)/3
2429 reflections	(Δ/σ)_max < 0.001
129 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₉H₉NO₃S	V = 982.46 (10) Å³
M_r = 211.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.4559 (5) Å	µ = 0.31 mm⁻¹
b = 7.5484 (5) Å	T = 296 K
c = 12.9408 (7) Å	0.19 × 0.18 × 0.09 mm
β = 105.863 (2)°

Data collection top

Bruker APEXII CCD diffractometer	1822 reflections with I > 2σ(I)
9319 measured reflections	R_int = 0.081
2429 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.08	Δρ_max = 0.34 e Å⁻³
2429 reflections	Δρ_min = −0.35 e Å⁻³
129 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.45672 (5)	0.21780 (7)	0.19351 (3)	0.0544 (2)
O1	0.27985 (14)	0.1334 (2)	−0.09326 (10)	0.0684 (5)
O2	0.50046 (15)	0.0632 (2)	0.25648 (10)	0.0770 (6)
O3	0.42257 (17)	0.3675 (2)	0.24709 (11)	0.0771 (6)
N1	0.33045 (15)	0.1647 (2)	0.08810 (12)	0.0540 (5)
C1	0.55956 (17)	0.2745 (2)	0.11296 (13)	0.0442 (5)
C2	0.68739 (19)	0.3429 (3)	0.14490 (15)	0.0568 (6)
C3	0.74791 (19)	0.3782 (3)	0.06576 (17)	0.0620 (6)
C4	0.68513 (19)	0.3479 (3)	−0.04052 (16)	0.0591 (7)
C5	0.55651 (19)	0.2815 (2)	−0.07236 (14)	0.0515 (6)
C6	0.49424 (17)	0.2447 (2)	0.00599 (13)	0.0417 (5)
C7	0.35743 (17)	0.1749 (2)	−0.00979 (13)	0.0473 (5)
C8	0.2068 (2)	0.0906 (3)	0.10313 (19)	0.0704 (8)
C9	0.0967 (3)	0.2234 (3)	0.0851 (3)	0.0977 (13)
H2	0.73010	0.36390	0.21690	0.0680*
H3	0.83380	0.42380	0.08450	0.0740*
H4	0.72950	0.37220	−0.09210	0.0710*
H5	0.51370	0.26240	−0.14450	0.0620*
H8A	0.22420	0.04450	0.17560	0.0840*
H8B	0.17840	−0.00750	0.05380	0.0840*
H9A	0.12320	0.31940	0.13500	0.1470*
H9B	0.01870	0.16790	0.09560	0.1470*
H9C	0.07780	0.26810	0.01300	0.1470*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0641 (3)	0.0629 (4)	0.0381 (3)	0.0102 (2)	0.0174 (2)	0.0029 (2)
O1	0.0600 (8)	0.0833 (10)	0.0532 (8)	−0.0087 (7)	0.0010 (6)	−0.0090 (7)
O2	0.0932 (11)	0.0822 (10)	0.0543 (8)	0.0116 (9)	0.0179 (7)	0.0255 (7)
O3	0.0937 (11)	0.0869 (10)	0.0586 (8)	0.0168 (9)	0.0343 (8)	−0.0156 (8)
N1	0.0505 (8)	0.0625 (9)	0.0515 (8)	0.0006 (7)	0.0181 (7)	0.0040 (7)
C1	0.0481 (9)	0.0458 (9)	0.0371 (8)	0.0107 (7)	0.0092 (7)	−0.0022 (6)
C2	0.0524 (10)	0.0596 (11)	0.0503 (10)	0.0075 (8)	0.0001 (8)	−0.0070 (8)
C3	0.0456 (9)	0.0604 (11)	0.0789 (13)	0.0027 (8)	0.0150 (9)	−0.0019 (10)
C4	0.0577 (11)	0.0601 (11)	0.0665 (12)	0.0051 (9)	0.0287 (9)	0.0037 (9)
C5	0.0611 (11)	0.0547 (10)	0.0406 (8)	0.0067 (8)	0.0172 (8)	−0.0013 (7)
C6	0.0464 (8)	0.0406 (8)	0.0372 (8)	0.0068 (7)	0.0098 (6)	−0.0015 (6)
C7	0.0484 (9)	0.0475 (9)	0.0439 (9)	0.0047 (7)	0.0092 (7)	−0.0008 (7)
C8	0.0610 (12)	0.0704 (14)	0.0886 (14)	−0.0035 (10)	0.0356 (11)	0.0074 (11)
C9	0.0638 (14)	0.0892 (18)	0.149 (3)	0.0057 (13)	0.0440 (17)	0.0024 (17)

Geometric parameters (Å, º) top

S1—O2	1.4252 (15)	C5—C6	1.375 (3)
S1—O3	1.4214 (16)	C6—C7	1.485 (3)
S1—N1	1.6673 (16)	C8—C9	1.496 (4)
S1—C1	1.7432 (18)	C2—H2	0.9300
O1—C7	1.202 (2)	C3—H3	0.9300
N1—C7	1.373 (2)	C4—H4	0.9300
N1—C8	1.470 (3)	C5—H5	0.9300
C1—C2	1.386 (3)	C8—H8A	0.9700
C1—C6	1.384 (2)	C8—H8B	0.9700
C2—C3	1.369 (3)	C9—H9A	0.9600
C3—C4	1.372 (3)	C9—H9B	0.9600
C4—C5	1.388 (3)	C9—H9C	0.9600

O2—S1—O3	117.14 (8)	N1—C7—C6	109.03 (14)
O2—S1—N1	109.24 (8)	N1—C8—C9	113.06 (19)
O2—S1—C1	112.89 (9)	C1—C2—H2	121.00
O3—S1—N1	109.99 (9)	C3—C2—H2	122.00
O3—S1—C1	112.01 (9)	C2—C3—H3	119.00
N1—S1—C1	92.85 (8)	C4—C3—H3	119.00
S1—N1—C7	115.14 (13)	C3—C4—H4	119.00
S1—N1—C8	120.78 (13)	C5—C4—H4	119.00
C7—N1—C8	123.60 (16)	C4—C5—H5	121.00
S1—C1—C2	127.97 (13)	C6—C5—H5	121.00
S1—C1—C6	109.98 (13)	N1—C8—H8A	109.00
C2—C1—C6	122.05 (16)	N1—C8—H8B	109.00
C1—C2—C3	117.03 (17)	C9—C8—H8A	109.00
C2—C3—C4	121.7 (2)	C9—C8—H8B	109.00
C3—C4—C5	121.14 (19)	H8A—C8—H8B	108.00
C4—C5—C6	118.02 (17)	C8—C9—H9A	109.00
C1—C6—C5	120.07 (17)	C8—C9—H9B	109.00
C1—C6—C7	112.86 (15)	C8—C9—H9C	109.00
C5—C6—C7	127.07 (15)	H9A—C9—H9B	110.00
O1—C7—N1	123.80 (17)	H9A—C9—H9C	109.00
O1—C7—C6	127.17 (16)	H9B—C9—H9C	110.00

O2—S1—N1—C7	−111.89 (13)	C7—N1—C8—C9	−85.9 (3)
O2—S1—N1—C8	60.49 (17)	C2—C1—C6—C7	−178.70 (16)
O3—S1—N1—C7	118.24 (13)	S1—C1—C6—C5	179.56 (13)
O3—S1—N1—C8	−69.38 (17)	S1—C1—C2—C3	−179.53 (16)
C1—S1—N1—C7	3.57 (13)	C6—C1—C2—C3	−0.8 (3)
C1—S1—N1—C8	175.95 (15)	S1—C1—C6—C7	0.24 (17)
O2—S1—C1—C2	−70.93 (19)	C2—C1—C6—C5	0.6 (3)
O2—S1—C1—C6	110.22 (13)	C1—C2—C3—C4	0.2 (3)
O3—S1—C1—C2	63.88 (19)	C2—C3—C4—C5	0.7 (3)
O3—S1—C1—C6	−114.97 (13)	C3—C4—C5—C6	−0.8 (3)
N1—S1—C1—C2	176.79 (18)	C4—C5—C6—C7	179.41 (17)
N1—S1—C1—C6	−2.06 (13)	C4—C5—C6—C1	0.2 (2)
S1—N1—C7—O1	176.40 (14)	C5—C6—C7—N1	−177.04 (16)
C8—N1—C7—O1	4.3 (3)	C1—C6—C7—O1	−178.07 (17)
S1—N1—C7—C6	−3.89 (17)	C1—C6—C7—N1	2.23 (19)
C8—N1—C7—C6	−176.03 (16)	C5—C6—C7—O1	2.7 (3)
S1—N1—C8—C9	102.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.37	3.265 (2)	162
C3—H3···O2ⁱⁱ	0.93	2.53	3.295 (3)	140
C8—H8A···O3ⁱⁱⁱ	0.97	2.45	3.139 (3)	128

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₉H₉NO₃S
M_r	211.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.4559 (5), 7.5484 (5), 12.9408 (7)
β (°)	105.863 (2)
V (Å³)	982.46 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.19 × 0.18 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9319, 2429, 1822
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.144, 1.08
No. of reflections	2429
No. of parameters	129
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.35

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.37	3.265 (2)	162
C3—H3···O2ⁱⁱ	0.93	2.53	3.295 (3)	140
C8—H8A···O3ⁱⁱⁱ	0.97	2.45	3.139 (3)	128

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

The authors are grateful to the Higher Education Commission (HEC), Pakistan, for providing funds for the single-crystal XRD facilities at GC University, Lahore.

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